Skip to content
Go to Home Page
News

Southwest Airlines: St. Thomas flights begin in February from 2 cities

July 29, 2025
•
5 min read
Westin Frenchman's Reef
The cards we feature here are from partners who compensate us when you are approved through our site, and this may impact how or where these products appear. We don’t cover all available credit cards, but our analysis, reviews, and opinions are entirely from our editorial team. Terms apply to the offers listed on this page. Please view our advertising policy and product review methodology for more information.

Picture this: It’s the middle of winter, and you’ve just boarded a two- or three-hour flight to the Caribbean — and you don’t even need a passport.

That will soon be the reality for two U.S. cities that are set to get brand-new Southwest Airlines flights to the U.S. Virgin Islands.

Starting in February, Southwest will fly nonstop to St. Thomas’ Cyril E. King Airport (STT) from two of its busiest East Coast bases: Baltimore/Washington International Thurgood Marshall Airport (BWI) and Orlando International Airport (MCO).

Southwest's 2 new St. Thomas flights

Southwest’s new MCO-STT service is first up, launching on Feb. 5. The new flight will make St. Thomas the first new destination for the Dallas-based carrier in almost five years; you have to go back to its 2021 Syracuse, New York, service (later canceled) to find the last time Southwest launched a new city.

And with all due respect to Syracuse, St. Thomas is a far more alluring mid-winter destination — one that boasts an array of resorts that you can book using points.

Marriott breathes new life into a beloved Caribbean resort: A review of The Westin Beach Resort & Spa at Frenchman's Reef

Westin Frenchman's Reef in St. Thomas, U.S. Virgin Islands. ELLIE NAN STORCK/THE POINTS GUY

Southwest’s flights between Orlando and St. Thomas will run daily all year long.

Meanwhile, flights to the island from BWI will launch on Feb. 7.

St. Thomas isn’t the end of Southwest’s expansion. Earlier this month, TPG reported the carrier had plans to announce two additional all-new cities as it begins expanding its route network, again, after uncharacteristic cuts last year. No word yet, however, on what or when those other two cities might be announced.

Daily Newsletter
Reward your inbox with the TPG Daily newsletter
Join over 700,000 readers for breaking news, in-depth guides and exclusive deals from TPG’s experts

Southwest assigned seats now for sale

The announcement of BWI and MCO flights to STT came the same day Southwest started selling assigned seats for the first time, on Tuesday. Those seat assignments (including its brand-new extra legroom seats) will apply to bookings made from Jan. 27, 2026 onward — including these new Caribbean routes.

Keep in mind, Southwest’s basic fares do not come with complimentary seat selection unless you have Rapid Rewards elite status or carry one of its cobranded credit cards.

Read more: 1 in 4 Southwest planes now have extra-legroom seats — Here's how to snag one

Southwest plane
Southwest Airlines aircraft at Dallas Love Field (DAL). DAVID SLOTNICK/THE POINTS GUY

Southwest’s new Choice fare comes with standard seat selection. Choice Preferred gives you access to a normal seat closer to the front of the plane, while Choice Extra gets you access to the extra legroom seats (not to mention two free checked bags).

Keep in mind, all Southwest credit cards now come with some form of seat selection (even on basic fares) and a free checked bag for the primary cardholder and up to eight companions flying on the same reservation.

Read more: Southwest unveils big credit card refresh: 50% fee hikes, but new seating and boarding perks

Beach, warm weather and ski destinations highlight returning winter routes

Beyond announcing two new St. Thomas routes, Southwest opened up its schedule for booking through March 4, 2026, and confirmed the (expected) return of 24 seasonal routes, effective Jan. 27.

Those include:

  • Chicago’s O’Hare International Airport (ORD) to Cancun international Airport (CUN)
  • ORD to Denver International Airport (DEN)
  • ORD to Fort Myers’ Southwest Florida International Airport (RSW)
  • Fort Lauderdale-Hollywood International Airport (FLL) to Rhode Island T. F. Green International Airport (PVD)
  • Albany International Airport (ALB) to RSW
  • ALB to Sarasota Bradenton International Airport (SRQ)
  • Austin-Bergstrom International Airport (AUS) to Luis Muñoz Marín International Airport (SJU)
  • Hartford’s Bradley International Airport (BDL) to RSW
  • Nashville International Airport (BNA) to Colorado’s Yampa Valley Regional Airport (HDN)
  • BNA to Punta Cana International Airport (PUJ)
  • Boston Logan International Airport (BOS) to MCO
  • Buffalo Niagara International Airport (BUF) to Palm Beach International Airport (PBI)
  • BWI to Providenciales International Airport (PLS) in Turks and Caicos
  • Dallas Love Field (DAL) to Palm Springs International Airport (PSP)
  • Detroit Wayne County Metropolitan Airport (DTW) to Phoenix Sky Harbor International Airport (PHX)
  • Long Island MacArthur Airport (ISP) to FLL
  • Houston's William P. Hobby Airport Airport (HOU) to Sangster International Airport (MBJ) in Montego Bay, Jamaica
  • HOU to SRQ
  • New York’s LaGuardia Airport (LGA) to Tampa International Airport (TPA)
  • Portland International Jetport (PWM) in Maine to MCO
  • Salt Lake City International Airport (SLC) to MCO
  • Tulsa International Airport (TUL) to MCO
  • Chicago’s Midway Airport (MDW) to PSP
  • Milwaukee Mitchell International Airport (MKE) to Miami International Airport (MIA)
  • PVD to PBI
  • Frederick Douglass Greater Rochester International Airport (ROC) to RSW
  • Louisville Muhammad Ali International Airport (SDF) to RSW

Many of these routes will operate with less-than-daily service to prime warm-weather, beach (and skiing) destinations during the cold winter months.

Related reading:

Featured image by ELLIE NAN STORCK/THE POINTS GUY
Editorial disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airline or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

TPG featured card

Best for dining at restaurants

American Express® Gold Card

Apply for American Express® Gold Card
Terms & restrictions apply. See rates & fees
TPG Editor‘s Rating
4 / 5
Go to review
Apply for American Express® Gold Card
at American Express's secure site

Rewards

1 - 4X points

Intro offer

As High As 100,000 points. Find Out Your Offer.

Annual Fee

$325

Recommended Credit

Excellent to Good

Why We Chose It

There’s a lot to love about the Amex Gold. It’s a fan favorite thanks to its fantastic bonus-earning rates at restaurants worldwide and at U.S. supermarkets. If you’re hitting the skies soon, you’ll also earn bonus Membership Rewards points on travel. Paired with up to $120 in Uber Cash annually (for U.S. Uber rides or Uber Eats orders, card must be added to Uber app and you can redeem with any Amex card), up to $120 in annual dining statement credits to be used with eligible partners, an up to $84 Dunkin’ credit each year at U.S. Dunkin Donuts and an up to $100 Resy credit annually, there’s no reason that foodies shouldn’t add the Amex Gold to their wallet. These benefits alone are worth more than $400, which offsets the $325 annual fee on the Amex Gold card. Enrollment is required for select benefits. (Partner offer)

Pros

  • 4 points per dollar spent on dining at restaurants worldwide and U.S. supermarkets (on the first $50,000 in purchases per calendar year; then 1 point per dollar spent thereafter and $25,000 in purchases per calendar year; then 1 point per dollar spent thereafter, respectively)
  • 3 points per dollar spent on flights booked directly with the airline or with amextravel.com
  • Packed with credits foodies will enjoy
  • Solid welcome bonus

Cons

  • Not as useful for those living outside the U.S.
  • Some may have trouble using Uber and other dining credits
  • You may be eligible for as high as 100,000 Membership Rewards® Points after you spend $6,000 in eligible purchases on your new Card in your first 6 months of Card Membership. Welcome offers vary and you may not be eligible for an offer. Apply to know if you’re approved and find out your exact welcome offer amount – all with no credit score impact. If you’re approved and choose to accept the Card, your score may be impacted.
  • Earn 4X Membership Rewards® points per dollar spent on purchases at restaurants worldwide, on up to $50,000 in purchases per calendar year, then 1X points for the rest of the year.
  • Earn 4X Membership Rewards® points per dollar spent at US supermarkets, on up to $25,000 in purchases per calendar year, then 1X points for the rest of the year.
  • Earn 3X Membership Rewards® points per dollar spent on flights booked directly with airlines or on AmexTravel.com.
  • Earn 2X Membership Rewards® points per dollar spent on prepaid hotels and other eligible purchases booked on AmexTravel.com.
  • Earn 1X Membership Rewards® point per dollar spent on all other eligible purchases.
  • $120 Uber Cash on Gold: Add your Gold Card to your Uber account and get $10 in Uber Cash each month to use on orders and rides in the U.S. when you select an American Express Card for your transaction. That’s up to $120 Uber Cash annually. Plus, after using your Uber Cash, use your Card to earn 4X Membership Rewards® points for Uber Eats purchases made with restaurants or U.S. supermarkets. Point caps and terms apply.
  • $84 Dunkin' Credit: With the $84 Dunkin' Credit, you can earn up to $7 in monthly statement credits after you enroll and pay with the American Express® Gold Card at U.S. Dunkin' locations. Enrollment is required to receive this benefit.
  • $100 Resy Credit: Get up to $100 in statement credits each calendar year after you pay with the American Express® Gold Card to dine at U.S. Resy restaurants or make other eligible Resy purchases. That's up to $50 in statement credits semi-annually. Enrollment required.
  • $120 Dining Credit: Satisfy your cravings, sweet or savory, with the $120 Dining Credit. Earn up to $10 in statement credits monthly when you pay with the American Express® Gold Card at Grubhub, The Cheesecake Factory, Goldbelly, Wine.com, and Five Guys. Enrollment required.
  • Explore over 1,000 upscale hotels worldwide with The Hotel Collection and receive a $100 credit towards eligible charges* with every booking of two nights or more through AmexTravel.com. *Eligible charges vary by property.
  • No Foreign Transaction Fees.
  • Annual Fee is $325.
  • Terms Apply.
Apply for American Express® Gold Card
at American Express's secure site
Terms & restrictions apply. See rates & fees
Best for dining at restaurants

American Express® Gold Card

TPG Editor‘s Rating
4 / 5
Go to review

Rewards Rate

4XEarn 4X Membership Rewards® points per dollar spent on purchases at restaurants worldwide, on up to $50,000 in purchases per calendar year, then 1X points for the rest of the year.
4XEarn 4X Membership Rewards® points per dollar spent at US supermarkets, on up to $25,000 in purchases per calendar year, then 1X points for the rest of the year.
3XEarn 3X Membership Rewards® points per dollar spent on flights booked directly with airlines or on AmexTravel.com.
2XEarn 2X Membership Rewards® points per dollar spent on prepaid hotels and other eligible purchases booked on AmexTravel.com.
1XEarn 1X Membership Rewards® point per dollar spent on all other eligible purchases.

  • Intro Offer

    As High As 100,000 points. Find Out Your Offer.

  • Annual Fee

    $325

  • Recommended Credit

    Excellent to Good

Why We Chose It

There’s a lot to love about the Amex Gold. It’s a fan favorite thanks to its fantastic bonus-earning rates at restaurants worldwide and at U.S. supermarkets. If you’re hitting the skies soon, you’ll also earn bonus Membership Rewards points on travel. Paired with up to $120 in Uber Cash annually (for U.S. Uber rides or Uber Eats orders, card must be added to Uber app and you can redeem with any Amex card), up to $120 in annual dining statement credits to be used with eligible partners, an up to $84 Dunkin’ credit each year at U.S. Dunkin Donuts and an up to $100 Resy credit annually, there’s no reason that foodies shouldn’t add the Amex Gold to their wallet. These benefits alone are worth more than $400, which offsets the $325 annual fee on the Amex Gold card. Enrollment is required for select benefits. (Partner offer)

Pros

  • 4 points per dollar spent on dining at restaurants worldwide and U.S. supermarkets (on the first $50,000 in purchases per calendar year; then 1 point per dollar spent thereafter and $25,000 in purchases per calendar year; then 1 point per dollar spent thereafter, respectively)
  • 3 points per dollar spent on flights booked directly with the airline or with amextravel.com
  • Packed with credits foodies will enjoy
  • Solid welcome bonus

Cons

  • Not as useful for those living outside the U.S.
  • Some may have trouble using Uber and other dining credits
  • You may be eligible for as high as 100,000 Membership Rewards® Points after you spend $6,000 in eligible purchases on your new Card in your first 6 months of Card Membership. Welcome offers vary and you may not be eligible for an offer. Apply to know if you’re approved and find out your exact welcome offer amount – all with no credit score impact. If you’re approved and choose to accept the Card, your score may be impacted.
  • Earn 4X Membership Rewards® points per dollar spent on purchases at restaurants worldwide, on up to $50,000 in purchases per calendar year, then 1X points for the rest of the year.
  • Earn 4X Membership Rewards® points per dollar spent at US supermarkets, on up to $25,000 in purchases per calendar year, then 1X points for the rest of the year.
  • Earn 3X Membership Rewards® points per dollar spent on flights booked directly with airlines or on AmexTravel.com.
  • Earn 2X Membership Rewards® points per dollar spent on prepaid hotels and other eligible purchases booked on AmexTravel.com.
  • Earn 1X Membership Rewards® point per dollar spent on all other eligible purchases.
  • $120 Uber Cash on Gold: Add your Gold Card to your Uber account and get $10 in Uber Cash each month to use on orders and rides in the U.S. when you select an American Express Card for your transaction. That’s up to $120 Uber Cash annually. Plus, after using your Uber Cash, use your Card to earn 4X Membership Rewards® points for Uber Eats purchases made with restaurants or U.S. supermarkets. Point caps and terms apply.
  • $84 Dunkin' Credit: With the $84 Dunkin' Credit, you can earn up to $7 in monthly statement credits after you enroll and pay with the American Express® Gold Card at U.S. Dunkin' locations. Enrollment is required to receive this benefit.
  • $100 Resy Credit: Get up to $100 in statement credits each calendar year after you pay with the American Express® Gold Card to dine at U.S. Resy restaurants or make other eligible Resy purchases. That's up to $50 in statement credits semi-annually. Enrollment required.
  • $120 Dining Credit: Satisfy your cravings, sweet or savory, with the $120 Dining Credit. Earn up to $10 in statement credits monthly when you pay with the American Express® Gold Card at Grubhub, The Cheesecake Factory, Goldbelly, Wine.com, and Five Guys. Enrollment required.
  • Explore over 1,000 upscale hotels worldwide with The Hotel Collection and receive a $100 credit towards eligible charges* with every booking of two nights or more through AmexTravel.com. *Eligible charges vary by property.
  • No Foreign Transaction Fees.
  • Annual Fee is $325.
  • Terms Apply.